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US20090299025A1 - Multi alkoxylated silicone surfactants - Google Patents

Multi alkoxylated silicone surfactants Download PDF

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US20090299025A1
US20090299025A1 US12/157,948 US15794808A US2009299025A1 US 20090299025 A1 US20090299025 A1 US 20090299025A1 US 15794808 A US15794808 A US 15794808A US 2009299025 A1 US2009299025 A1 US 2009299025A1
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silicone compound
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Kevin Anthony O'Lenick
Anthony J. OLenick, JR.
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Siltech Corp
Siltech Inc
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/42—Block-or graft-polymers containing polysiloxane sequences
    • C08G77/46—Block-or graft-polymers containing polysiloxane sequences containing polyether sequences
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/38—Polysiloxanes modified by chemical after-treatment

Definitions

  • the present invention is directed to organo-silicone compound that have alkoxylated allyl alcohol groups of different degree of ethylene oxide and or propylene oxide present on two or more different groups. It is also directed to the use of that compound in personal care and other applications. These compounds by virtue of their unique structure provide outstanding emulsions including microemulsions.
  • Organofunctional silicone compounds are one of two types, internal and terminal depending upon the location of the silicone group.
  • terminal group has the organic functional groups at the alpha and omega terminus of the molecule.
  • Typical; of this class of compounds is the class of compounds currently called bis-dimethicone conforming to the following structure:
  • comb structure in which the organofunctionality is located on non-terminal ends of the molecule.
  • This type of compound is called a “comb” compound since the organofunctionality lies in the molecule much like the teeth of a comb.
  • the present invention is directed to compounds in of the comb type having two different “R” groups. Such compounds have been disclosed in the so-called comb alkyl dimethicone copolyol class.
  • R 1 is —(CH 2 ) 3 —O—(CH 2 CH 2 O) 8 H and R 2 is —(CH 2 ) 11 —CH 3
  • the compound is lauryl PEG-8 dimethicone.
  • Such compounds are known and U.S. Pat. No. 7,279,503 to O'Lenick, incorporated herein by reference, is typical of patents related to such compounds. These compounds have two different types of compounds present on the molecule, in this case alkyl and alkoxylated.
  • the object present invention a series of silicone polymers containing two different alkoxylated groups on the same molecule together. These materials have outstanding surfactant properties and are therefore useful in personal care applications. Other objects will become clear by reading the specification.
  • the compounds of the present invention are prepared by the reaction of a silanic hydrogen containing silicone polymer conforming to the following structure:
  • x+y+z is zero and t+u+v is equal to or greater than 10.
  • x+y+z are less than 5 and t+u+v is equal to or greater than 10.
  • q is zero and x+y+z is zero and t+u+v is equal to or greater than 10.
  • q is 1 or greater embodiment x+y+z are less than 5 and t+u+v is equal to or greater than 10.
  • q is zero and x+y+z is zero and t+u+v is equal to or greater than 10 and s is less than or equal to 7.
  • q is 1 or greater embodiment x+y+z are less than 5 and t+u+v is equal to or greater than 10 and s is less than or equal to 17.
  • q is zero and x+y+z is zero and t+u+v is equal to or greater than 10 and s is greater than or equal to 19.
  • q is 1 or greater embodiment x+y+z are less than 5 t+u+v is equal to or greater than 10 and s is greater than or equal to 19.
  • Alpha olefins are commercially available form a variety of sources including Chevron. They conform to the following structure:
  • Allyl alcohol alkoxylates are commercially available from several sources including Dow Chemical, Ethox Chemical, Siltech Corporation and KAO Chemical. They conform to the following structure:
  • x, y, and z are independently integers ranging from 0 to 5, with the proviso x+y+z is less than or equal to 5.
  • allyl alcohol alkoxylates of class 2 are commercially available from several sources including Dow Chemical, Ethox Chemical, Siltech Corporation and KAO Chemical. They conform to the following structure
  • t, u and v are independently integers ranging from 0 to 20 with the proviso t+u+v are than or equal to 10;
  • the specified number of grams of allyl alcohol alkoxylates Class 1 (examples 13-17) and the specified number of grams of the specified allyl alcohol alkoxylate Class 2 (examples 18-20) are added to a vessel having agitation and cooling.
  • the specified number of grams of silanic hydrogen (examples 1 -10) and specified number of gram of alpha olefin (examples 11-16) is added, following by the specified number of grams of anhydrous isopropanol.
  • the batch is then heated until the alpha olefin is liquid, or 80 C whichever is lower.
  • 20 ppm Karnstedt catalyst (based upon the weight of all materials to be added) is added. Cooling is added to control the exotherm. It is not uncommon for the temperature to rise from 80 C to 90 C. Hold at 120 C for 4 hours, checking the Silanic hydrogen content until it becomes vanishing small. Distill off isopropanol using vacuum.
  • the first set of experiments are conducted using all four emulsifiers, and allow the formulator not only the ability to evaluate emulsion stability, but also cosmetic aesthetics.
  • the formulation is:

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Silicon Polymers (AREA)
  • Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)

Abstract

The present invention is directed to organo-silicone compound that have alkoxylated allyl alcohol groups of different degree of ethylene oxide and or propylene oxide present on two or more different groups. It is also directed to the use of that compound in personal care and other applications. These compounds by virtue of their unique structure provide outstanding emulsions including microemulsions.

Description

    RELATED APPLICATIONS
  • This application claims priority to and benefit of U.S. Provisional Application No. 61/128,798 filed May 27, 2008, the disclosure of which is incorporated herein for all purposes.
    • FIELD OF THE INVENTION
  • The present invention is directed to organo-silicone compound that have alkoxylated allyl alcohol groups of different degree of ethylene oxide and or propylene oxide present on two or more different groups. It is also directed to the use of that compound in personal care and other applications. These compounds by virtue of their unique structure provide outstanding emulsions including microemulsions.
    • BACKGROUND OF THE INVENTION
  • Organofunctional silicone compounds are one of two types, internal and terminal depending upon the location of the silicone group.
  • The so-called terminal group has the organic functional groups at the alpha and omega terminus of the molecule. Typical; of this class of compounds is the class of compounds currently called bis-dimethicone conforming to the following structure:
  • Figure US20090299025A1-20091203-C00001
  • In the case where R is —(CH2)3—O—(CH2CH2O)8H the compound is bis PEG-8 dimethicone.
  • The other type of compound is referred to as comb structure in which the organofunctionality is located on non-terminal ends of the molecule. This type of compound is called a “comb” compound since the organofunctionality lies in the molecule much like the teeth of a comb. These compounds are shown in the following structure:
  • Figure US20090299025A1-20091203-C00002
  • In the case where R is —(CH2)3—O—(CH2CH2O)8H the compound is simply PEG-8 dimethicone.
  • The present invention is directed to compounds in of the comb type having two different “R” groups. Such compounds have been disclosed in the so-called comb alkyl dimethicone copolyol class.
  • Figure US20090299025A1-20091203-C00003
  • In the case where R1 is —(CH2)3—O—(CH2CH2O)8H and R2 is —(CH2)11—CH3 the compound is lauryl PEG-8 dimethicone. Such compounds are known and U.S. Pat. No. 7,279,503 to O'Lenick, incorporated herein by reference, is typical of patents related to such compounds. These compounds have two different types of compounds present on the molecule, in this case alkyl and alkoxylated.
  • We have surprisingly found that when two different level of alkoxylation are placed on one molecule the surfactant properties of the resulting emulsifier can be improved. None of the prior art known to us disclose such a compound.
    • THE INVENTION OBJECT OF THE INVENTION
  • The object present invention a series of silicone polymers containing two different alkoxylated groups on the same molecule together. These materials have outstanding surfactant properties and are therefore useful in personal care applications. Other objects will become clear by reading the specification.
    • DETAILED DESCRIPTION OF THE INVENTION
  • The compounds of the present invention conform to the following structure:
  • Figure US20090299025A1-20091203-C00004
  • wherein;
    • R3 is —(CH2)3—O—(CH2CH2O)x—(CH2CH(CH3)O)y—(CH2CH2O)zH;
    • R4 is —(CH2)3—O—(CH2CH2O)t—(CH2CH(CH3)O)u—(CH2CH2O)vH;
    • s is an integer ranging from 11 to 25;
    • x, y and z are independently integers ranging from 0 to 20;
    • t, u, and v are independently integers ranging from 0 to 20, with the proviso x does not equal t, and y does not equal u and z does not equal v (that is that the alkoxylate groups are not identical)
    • m is an integer ranging from 0 to 200;
    • n is an integer ranging from 1 to 20;
    • p is an integer ranging from 1 to 20;
    • q is an integer ranging from 0 to 20.
  • The compounds of the present invention are prepared by the reaction of a silanic hydrogen containing silicone polymer conforming to the following structure:
  • Figure US20090299025A1-20091203-C00005
  • wherein:
    • and an “q” moles of alpha olefinic containing polymer selected from the group consisting of:

  • CH2═CH—(CH2)s−2—CH3;
    • “n” moles of the first alkoxylate conforming to the following structure:

  • CH2═CH—CH2—O—(CH2CH2O)x—(CH2CH(CH3)—O)y—(CH2CH2O)z—H
  • and
    • “p” moles of the first alkoxylate conforming to the following structure:

  • CH2═CH—CH2—O—(CH2CH2O)t—(CH2CH(CH3)—O)u—(CH2CH2O)v—H
    • s is an integer ranging from 11 to 25;
    • t, u and v are independently integers ranging from 0 to 20;
    • x, y, and z are independently integers ranging from 0 to 5, with the proviso x+y+z is less than or equal to 5 and t+u+v are greater than or equal to 10;
    • m is an integer ranging from 0 to 200;
    • n is an integer ranging from 1 to 20;
    • p is an integer ranging from 1 to 20;
    • q is an integer ranging from 0 to 20.
    Preferred Embodiment
  • In a preferred embodiment x+y+z is zero and t+u+v is equal to or greater than 10.
  • In a preferred embodiment x+y+z are less than 5 and t+u+v is equal to or greater than 10.
  • In a preferred embodiment q is zero and x+y+z is zero and t+u+v is equal to or greater than 10.
  • In a preferred embodiment q is 1 or greater embodiment x+y+z are less than 5 and t+u+v is equal to or greater than 10.
  • In a preferred embodiment q is zero and x+y+z is zero and t+u+v is equal to or greater than 10 and s is less than or equal to 7.
  • In a preferred embodiment q is 1 or greater embodiment x+y+z are less than 5 and t+u+v is equal to or greater than 10 and s is less than or equal to 17.
  • In a preferred embodiment q is zero and x+y+z is zero and t+u+v is equal to or greater than 10 and s is greater than or equal to 19.
  • In a preferred embodiment q is 1 or greater embodiment x+y+z are less than 5 t+u+v is equal to or greater than 10 and s is greater than or equal to 19.
    • EXAMPLES
  • Silanic Hydrogen Compounds
  • Silanic hydrogen compounds conform to the following structure:
  • Figure US20090299025A1-20091203-C00006
  • wherein;
    • m is an integer ranging from 0 to 200;
    • n is an integer ranging from 1 to 20;
    • p is an integer ranging from 1 to 20;
    • q is an integer ranging from 0 to 20.
  • They are commercially available from Siltech LLC of Dacula, Ga. The specific values reported below for the molecule were determined by Si-29 nmr.
  • Example m n p q n + p + q
    1 0 1 5 1 7
    2 4 5 1 5 11
    3 10 4 10 0 14
    4 20 3 10 10 23
    5 40 10 20 10 40
    6 50 20 5 5 30
    7 15 5 2 20 27
    8 20 15 15 6 36
    9 100 20 5 1 26
    10 200 20 20 0 40
  • Olefinic Compounds
  • Alpha olefins are commercially available form a variety of sources including Chevron. They conform to the following structure:

  • CH2═CH—(CH2)s−2—CH3;
  • Example s
    11 9
    12 11
    13 23
    14 20
    15 25
  • Allyl Alcohol Alkoxylates
  • Class 1
  • Allyl alcohol alkoxylates are commercially available from several sources including Dow Chemical, Ethox Chemical, Siltech Corporation and KAO Chemical. They conform to the following structure:

  • CH2═CH—CH2—O—(CH2CH2O)x—(CH2CH(CH3)—O)y—(CH2CH2O)z—H
  • x, y, and z are independently integers ranging from 0 to 5, with the proviso x+y+z is less than or equal to 5.
  • Example x y z
    13 0 0 0
    14 1 1 1
    15 0 5 0
    16 2 0 2
    17 0 1 4
  • Class2
  • Likewise the allyl alcohol alkoxylates of class 2 are commercially available from several sources including Dow Chemical, Ethox Chemical, Siltech Corporation and KAO Chemical. They conform to the following structure

  • CH2═CH—CH2—O—(CH2CH2O)t—(CH2CH(CH3)—O)u—(CH2CH2O)v—H
  • t, u and v are independently integers ranging from 0 to 20 with the proviso t+u+v are than or equal to 10;
  • Example t u v
    18 20 20 20
    19 0 10 0
    20 10 0 0
    21 5 3 5
    22 20 2 5
    • PRODUCTS OF THE PRESENT INVENTION
  • General Procedure
  • The specified number of grams of allyl alcohol alkoxylates Class 1 (examples 13-17) and the specified number of grams of the specified allyl alcohol alkoxylate Class 2 (examples 18-20) are added to a vessel having agitation and cooling. Next the specified number of grams of silanic hydrogen (examples 1 -10) and specified number of gram of alpha olefin (examples 11-16) is added, following by the specified number of grams of anhydrous isopropanol. The batch is then heated until the alpha olefin is liquid, or 80 C whichever is lower. Next 20 ppm Karnstedt catalyst (based upon the weight of all materials to be added) is added. Cooling is added to control the exotherm. It is not uncommon for the temperature to rise from 80 C to 90 C. Hold at 120 C for 4 hours, checking the Silanic hydrogen content until it becomes vanishing small. Distill off isopropanol using vacuum.
  • Silanic Hydrogen Alkoxylate 1 Alkoxylate 2 Alpha Olefin Isopropanol
    Example Example Grams Example Grams Example Grams Example Grams Grams
    23 1 58 13 6 18 1500 11 14 20
    24 2 112 14 103 19 65 12 84 88
    25 3 174 15 141 20 500 13 0 163
    26 4 302 16 70 21 675 14 280 265
    27 5 664 17 294 22 2556 15 364 776
    28 6 566 13 118 18 1500 11 70 460
    29 7 289 14 100 19 130 12 336 200
    30 8 380 15 528 21 748 13 202 400
    31 9 912 16 470 22 337 14 28 450
    32 10 173 17 588 18 2556 15 0 610
  • Emulsion Formulation
  • The first set of experiments are conducted using all four emulsifiers, and allow the formulator not only the ability to evaluate emulsion stability, but also cosmetic aesthetics.
  • The formulation is:
  • Emulsifier Formula
    Material %
    Water 47.25
    Oil 47.25
    Emulsifier 5.00
    Salt 0.5
  • Procedure:
      • 1. Place emulsifier or emulsifier blend into the oil phase.
      • 2. Mix well, noting clarity.
      • 3. Add salt to water phase.
      • 4. Heat both phases to 50° C.
      • 5. Add water phase to oil phase and using mixer mix for 120 seconds.
      • 6. Note appearance.
  • A comparison was made using the above formulation. The emulsions that were formed using the products containing a high and a low allyl allyl alcohol were more stable than those made with a molecule having the same number of moles of ethylene oxide and propylene oxide together in one allyl alcohol group. The presence of a high and a low amount of polyoxyalkylene in two different groups on the silicone polymer gives stability to emulsions made using the polymer over a silicone emulsifier in which there is one allyl alcohol alkoxylate with the same average number of moles of alkoxylate present. The conclusion is that two different allyl alcohol alkoxylates, one with a high amount of EO/PO and the other with a low amount of EO/PO will give surprisingly different surfactant properties than if the molecule made with the same average content on one molecule. While not wanting to be held to one reason for this it appears that the allyl alcohol portion with the low degree of alkoxylation (EO/PO) is a low HLB material and the portion with a high degree of alkoxylation (EO/PO) is a high HLB material and that putting the two in one molecule a particularly potent intra-molecular HLB pair emulsifier results.
  • While the illustrative embodiments of the invention have been described with particularity, it will be understood that various other modifications will be apparent to and can be readily made by those skilled in the art without departing from the spirit and scope of the invention. Accordingly, it is not intended that the scope of the claims appended hereto be limited to the examples and descriptions set forth hereinabove but rather that the claims be construed as encompassing all the features of patentable novelty which reside in the present invention, including all features which would be treated as equivalents thereof by those skilled in the art to which the invention pertains.

Claims (18)

1. A silicone polymer conforming to the following structure:
Figure US20090299025A1-20091203-C00007
wherein;
R3 is —(CH2)3—O—(CH2CH2O)x—(CH2CH(CH3)O)y—(CH2CH2O)zH;
R4 is —(CH2)3—O—(CH2CH2O)t—(CH2CH(CH3)O)u—(CH2CH2O)vH;
s is an integer ranging from 11 to 25;
x, y and z are independently integers ranging from 0 to 20;
t, u, and v are independently integers ranging from 0 to 20, with the proviso x does not equal t, and y does not equal u and z does not equal v (that is that the alkoxylate groups are not identical)
m is an integer ranging from 0 to 200;
n is an integer ranging from 1 to 20;
p is an integer ranging from 1 to 20;
q is an integer ranging from 0 to 20.
2. A silicone compound of claim 1 wherein x+y+z is zero and t+u+v is equal to or greater than 10.
3. A silicone compound of claim 1 wherein x+y+z are less than 5 and t+u+v is equal to or greater than 10.
4. A silicone compound of claim 1 wherein q is zero and x+y+z is zero and t+u+v is equal to or greater than 10.
5. A silicone compound of claim 1 wherein q is 1 or greater embodiment x+y+z are less than 5 and t+u+v is equal to or greater than 10.
6. A silicone compound of claim 1 wherein q is zero and x+y+z is zero and t+u+v is equal to or greater than 10 and s is less than or equal to 17.
7. A silicone compound of claim 1 wherein q is 1 or greater embodiment x+y+z are less than 5 and t+u+v is equal to or greater than 10 and s is less than or equal to 17.
8. A silicone compound of claim 1 wherein q is zero and x+y+z is zero and t+u+v is equal to or greater than 10 and s is greater than or equal to 9.
9. A silicone compound of claim 1 wherein q is 1 or greater embodiment x+y+z are less than 5 and t+u+v is equal to or greater than 10 and s is greater than or equal to 19.
10. A silicone compound prepared by the reaction of
(a) a silanic hydrogen containing silicone polymer conforming to the following structure:
Figure US20090299025A1-20091203-C00008
wherein:
with
(b) q moles of alpha olefinic containing polymer selected from the group consisting of:

CH2═CH—(CH2)s−2—CH3;
(c) n moles of the first alkoxylate conforming to the following structure:

CH2═CH—CH2—O—(CH2CH2O)x—(CH2CH(CH3)—O)y—(CH2CH2O)z—H
and
(d)“p” moles of the first alkoxylate conforming to the following structure:

CH2═CH—CH2—O—(CH2CH2O)t—(CH2CH(CH3)—O)u—(CH2CH2O)v—H
s is an integer ranging from 11 to 25;
t, u and v are independently integers ranging from 0 to 20;
x, y, and z are independently integers ranging from 0 to 5, with the proviso x+y+z is less than or equal to 5 and t+u+v are greater than or equal to 10;
m is an integer ranging from 0 to 200;
n is an integer ranging from 1 to 20;
p is an integer ranging from 1 to 20;
q is an integer ranging from 0 to 20.
11. A silicone compound of claim 10 wherein x+y+z is zero and t+u+v is equal to or greater than 10.
12. A silicone compound of claim 10 wherein x+y+z are less than 5 and t+u+v is equal to or greater than 10.
13. A silicone compound of claim 10 wherein q is zero and x+y+z is zero and t+u+v is equal to or greater than 10.
14. A silicone compound of claim 10 wherein q is 1 or greater embodiment x+y+z are less than 5 and t+u+v is equal to or greater than 10.
15. A silicone compound of claim 10 wherein q is zero and x+y+z is zero and t+u+v is equal to or greater than 10 and s is less than or equal to 17.
16. A silicone compound of claim 10 wherein q is 1 or greater embodiment x+y+z are less than 5 and t+u+v is equal to or greater than 10 and s is less than or equal to 17.
17. A silicone compound of claim 10 wherein q is zero and x+y+z is zero and t+u+v is equal to or greater than 10 and s is greater than or equal to 9.
18. A silicone compound of claim 10 wherein q is 1 or greater embodiment x+y+z are less than 5 and t+u+v is equal to or greater than 10 and s is greater than or equal to
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